502618-02-2Relevant academic research and scientific papers
Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour
Jha, Amitabh,Paul, Nawal K.,Trikha, Smriti,Cameron, T. Stanley
, p. 843 - 853 (2006)
A novel two-step procedure involving the formation of 1-arylidene-2- tetralones from 2-tetralone and subsequent Michael addition of a cyclic secondary amine on the alkenone followed by in situ aerial oxidation was developed to produce 2-naphthol Mannich bases. A simple microwave-assisted one-pot synthesis of 2-naphthol Mannich bases was also carried out under solvent-free conditions from 2-naphthol and corresponding aldehydes and amines in the presence of p-toluenesulfonic acid. The compounds of this series displayed interesting NMR behaviour. Extensive variable-temperature NMR investigations, including HSQC experiments, are herein reported. NMR results on the conformation in solution phase were found to be consistent with the X-ray crystal structure in the solid state.
Experimental and theoretical investigations on acid catalysed stereoselective synthesis of new indazolyl-thiazole derivatives
Gautam, Poonam,Gautam, Deepika,Chaudhary
, p. 333 - 341 (2018)
1-Arylidene-2-tetralone (2), obtained from condensation of 2-tetralone and aromatic aldehydes in acetic acid and HCl, on condensation with thiosemicarbazide in acidic and alkaline medium afforded tetrahydro-2H-benzo[e]indazole-2-carbothioamide as trans (3) and cis (4) diastereoisomers of 1-H and 9b-H respectively. The synthesis of new indazolyl-thiazol-4(5H)-ones (5) from trans isomer (3) and α-halo acids is reported. A DFT study along with single crystal X-ray diffraction data of a representative compound (5a) is presented. The chemistry of the reaction of indazole-2-carbothioamides with methyl iodide, DMAD and acetic anhydride is described. Eight newly synthesised compounds were screened for their antibacterial and antifungal activities. Some of the compounds have shown promising antimicrobial activities.
Tandem Rh-Catalyzed [4 + 2] Vinylic C-H O-Annulation of Exocyclic Enones with Alkynes and 1,5-H Shift
Zhao, Yinsong,Yu, Chuangui,Wang, Tianbao,She, Zhijie,Zheng, Xuesong,You, Jingsong,Gao, Ge
supporting information, p. 1074 - 1077 (2018/02/23)
Active pyrylium intermediates are in situ generated by a Rh-catalyzed vinylic C-H annulation reaction between exocyclic α,β-enones and alkynes, which undergo a base-promoted rearrangement via 1,5-H shift to form 1H-benzo[f]chromene derivatives.
Cytotoxic 1,3-diarylidene-2-tetralones and related compounds
Dimmock, Jonathan R,Padmanilyam, Maniyan P,Zello, Gordon A,Wilson Quail,Oloo, Eliud O,Prisciak, Jared S,Kraatz, Heinz-Bernhard,Cherkasov, Arten,Lee, Jeremy S,Allen, Theresa M,Santos, Cheryl L,Manavathu, Elias K,De Clercq, Erik,Balzarini, Jan,Stables, James P
, p. 813 - 824 (2007/10/03)
A number of 1,3-arylidene-2-tetralones 1, 2 and 4 were synthesised and demonstrated cytotoxic activity towards murine P388 and L1210 cells as well as human Molt 4/C8 and CEM T-lymphocytes. In general, the related 1-arylidene-2-tetralones 3 possessed lower potencies in these screens than the compounds in series 1 and 4. Approximately, half of the compounds were evaluated against a panel of human tumour cell lines. In this screen, most of the enones were more cytotoxic than the established anticancer agent melphalan and some demonstrated selective toxicity towards leukemic and colon cancer cells. The modes of action of representative compounds include interfering with the biosyntheses of nucleic acids and proteins as well as altering redox potentials. The compounds were well tolerated when administered intraperiteonally to mice. Thus these novel enones are promising prototypic molecules due to their potent cytotoxic properties and lack of significant murine toxicity.
